Celebrity Style Evolution: Justin Timberlake

Phase I: Boy Meets Band

2000

At the dawn of 'NSync's No Strings Attached era, we find a young and impressionable JT. He has everything—a platinum-selling record, teenage biddies by the boatload, a puppet, bleached ramen noodle hair. Everything, and yet nothing at all.

2001

From JT's 2011 Playboy interview, an excerpt on fashion regrets:

"God, I feel I've gone to therapy just to erase some of them. The cornrows I wore with 'NSync. That was pretty bad. Britney and I wore matching denim outfits [to the 2001 American Music Awards]. Yeah, another bad choice. I'd probably pay good money to get some of those pictures off the Internet."

The Internet is forever, man. You will bear this sartorial mark of shame for all eternity!

2001

Justin questions his place in 'NSync. This is the face of a man who realized he just killed sexy and then accidently dropped a load on its grave. Where were we? Ah, right. Cool pants.

2003

'NSync disbands. A distraught Timberlake finds solace in the only other thing he loves besides singing: poor life choices. Also, who wore it better?

Phase II: Nicely Requesting the Return of Sexy

2006

Timberlake releases the excellent FutureSex/LoveSounds and stops looking like 'NSync's bitch. Yeah, the outfit's a little baggy, but awesome in comparison to his decade of style ruin.

Learning from follies of yore, JT pairs the fedora with a chocolate biker jacket and a contrast collar-skinny tie combo. The result: A gentleman, or someone we'd gladly call "Le Coq."

2009

"Motherlover," the sequel to "Dick in a Box" goes viral. He celebrates with a three-piece suit and some tie bling, but skimps on the tailor.

Phase III: Suck It Zuckerberg, I Am Sean Parker

2010

Three years into his career transition, Timberlake shines in The Social Network. The acting upgrade coincides with a mini-style renaissance, hence the chunky rims and razor-sharp lapels. Shortly after, he voices Boo-Boo in Yogi Bear. Bold choices, JT, bold choices.

2011

Justin loses the shades, adds a woman, and goes black-on-black-on-black-on-black. Yes, dude's a veritable style ninja, but think about what happened last time he brought a date to an awards show. Wait, don't, it burns.

2011

Scaling back the black, our man ends up with this natty look, compliments of the solo repp tie. OK, sweet, over a decade later, he's finally figured out the whole "wearing clothes that look good" thing.

Coinciding the release of the 20/20 Experience 2 of 2, Timberlake fully sheds the suited-up look he debuted earlier this year. Say hello to JT iOS7: master of color blocking and sick J's.

Photo: Getty Images

2013

Yeah, he penned a song called "Suit and Tie," but even JT knows the no-tie look is cool as hell. He nails it by pairing a paneled button-up with that navy tudo, which keeps things properly formal and fashion-forward. Well played.

Photo: Getty Images

2013

JT kicks off his solo tour for the 20/20 Experience and rocks the sartorial equivalent of his new album: a masterful, can't-f@#!k-with-this Tom Ford cream tux. Behold, the power of the Tom Ford upgrade.

At the dawn of 'NSync's No Strings Attached era, we find a young and impressionable JT. He has everything—a platinum-selling record, teenage biddies by the boatload, a puppet, bleached ramen noodle hair. Everything, and yet nothing at all.